1,2-Diaminocyclohexane, trans- → HCID 68782383, compound

HRID 80156Notes

Reaction equation

HRID 80156 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:16]=[C:17]2[CH:23]=[N:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:18]2=[N:19][CH:20]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([C:15]2[CH:16]=[C:17]3[CH:23]=[N:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:18]3=[N:19][CH:20]=2)[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 67078557HCID 67078557, compound

Product 1

HCID 68782383HCID 68782383, compoundYield 67.71%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 18, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 0.108 g, 0.0006 mol) was reacted with 5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (0.2 g, 0.0006 mol), 1,4-dioxane (20 mL), copper iodide (6.011 g, 0.00006 mol), trans-1,2-diamino cyclohexane (0.020 g, 0.00018 mol) and potassium phosphate (0.254 g, 0.0012 mol) to afford the crude product. Purification by column chromatography on silica gel (15% MeOH in CHCl3) afforded 172 mg of 1-(4-Methyl-pyridin-3-yl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-imidazolidin-2-one (67.71% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (15% MeOH in CHCl3)

Sources & evidence

ORD record
ord-5d495adbbb13469bb416f528f962026e
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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